Johann



UNITED STATES PATENT OFFICE.

JOHANN CARL XVILHELM FERDINAND TIEMANN, OF BERLIN, ASSIGNOR TO IIAARMANN& REIMER, OF IIOLZMINDEN, GERMANY.

PROCESS OF CONVERTlNG COMPOUNDS OF THE CITRAL SERIES INTO ISOMERS.

SPECIFICATION forming part of Letters Patent No. 556,944, dated March2.4, 1896.

A li ti fil d October 16, 1893. erial No. 488,322, (No specimens.)Patented in Germany geptember 8, 1893,1Tm 75,062; in Belgium S t b23,1893,N- 106,52l: in England October 11, 1893, No. 19,144,, and inFrance November 11, 1893, No

To aaZZ whom it may concern.-

Be it known that I, J OHANN CARL VIL- HELM FERDINAND TIEMANN,(coproprietor of the firm of Haarmann dz Reimer, of l-lolzmin- (1e11,) asubject of the King of Prussia, German Emperor, residing at Berlin, inthe Kingdom of Prussia and German Empire, have invented new and usefulImprovements in Processes of Converting Compounds of the ()itral Seriesinto Isomers, (for which I have obtained Letters Patent in Germany, N 0.75,062, dated September 8, 1893; in Belgium, No. 106,521, datedSeptember 23, 1893; in England, No. 19,144, dated Octoberll, 1893, andin France, No. 234,010, dated November 11, 1893,) of which the followingis a specification.

I have found that the compounds of the citral series (geranium series)are converted by the action of dilute sulfuric acid into isomers havinga higher specific gravity and a lower boiling-point than the originalbodies.

ELUCmtlJl I.-If, with shaking, oily geranium acid (O lL O is added toseventy per cent. sulfuric acid cooled to a temperature below zero, itis transformed into a solid isomeric acid, which, by pouring the mixtureinto water, extracting the dilute solution with other and crystallizingfrom water or ligroine, is obtained in pure crystals. The geranium acidis liquid. The crystallized isogeranium acid melts at 103.5. Thegeranium acid boils under a pressure of thirteen millimeters at atemperature of 153. The isogeranium acid dist-ills over under a pressureof eleven millimeters at a temperature of 138.

EzramgpicII-By exactly the same treatment the nitril of geranium acid (011 is transformed into the nitril of isogeraniuin acid.

Properties of the original body and of the product of conversion:

Erample III. -By heating in the waterbath the hydrocarbon obtained byseparating carbonic acid from geranium acid (gerani- Boiling-point atatmos- I Specific pheric pressure. gravity.

Geranidene 142-143 I. 4368 Isogcrsnidene 13S-140 1. 4434 The sulfuricacid may be replaced in the above-described conversions by other weakcondensing agents, such as phosphoric acid, metaphosphoric acid, &c.,which, as is commonly known, act in this respect in the same manner.However, by employing sulfuric acid I have obtained the best results.

The iso-compounds of the citral series (geranium series) are intended tobe used for perfum cry purposes.

W'hat I claim as new is A process for converting compounds of the citralseries (geranium series) into isomers having a lower boiling-point and ahigher specific gravity than the original bodies, which process consistsin subjecting the said compounds for some time to the action of dilutesulfuric acid, substantially as described.

In testimony whereof I have signed my name to this specification in thepresence of two subscribing witnesses.

J OHANN {JARL WILHELM FERDIXAND TIlllliiNN.

Witnesses:

GUSTAV HULSMANN,

Linn MTI LLER.

